Southeast Wisconsin Holidays from NZ$3,234

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The Latest Southeast Wisconsin Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was NZ$4,009, price is now NZ$3,234 per person
NZ$3,234
per person
5 Sept - 11 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
It needs to be refreshed it’s drab and dreary and doesn’t look clean my bathroom was dangerous I don’t need a handicap accessible but there are no bars to hang on to getting in and out of shower just depressing and breakfast a joke 1 morning no protein at all

Reviewed on 13 July 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$4,324, price is now NZ$3,433 per person
NZ$3,433
per person
5 Sept - 11 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Our stay at the Omni Chicago Hotel was great. Room was clean, the staff was outstanding and bar was great.

Reviewed on 14 July 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$4,833, price is now NZ$3,853 per person
NZ$3,853
per person
5 Sept - 11 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Awesome property. Enjoyed the lobby bar and the convenience to downtown area.

Reviewed on 14 July 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was NZ$4,532, price is now NZ$3,677 per person
NZ$3,677
per person
5 Sept - 11 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (2,239 reviews)
Great location near Park, museums, restaurants, River Walk, and theaters. Kudos to Gail and Alex at the Concierge Desk -- they were so very helpful, patient and kind.

Reviewed on 14 July 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$4,526, price is now NZ$3,710 per person
NZ$3,710
per person
5 Sept - 11 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
Hidden Fees!! Hidden Fees!! Hidden Fees!! *Know before you Go. Be prepared to accrue daily fees and taxes on site (separate from the taxes and fees paid to Expedia when booking). No pool. Room cleanliness could use a bit of work as I found a use bandaid between the bed and dresser. Otherwise the hotel is generally nice, it felt safe and in a great location with beautiful views.

Reviewed on 14 July 2026

Our guide on where to stay in Southeast Wisconsin

Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Wisconsin
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Southeast Wisconsin Holiday

Our pick of the best Southeast Wisconsin Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is NZ$392 per night from 20 July to 21 July
NZ$392
20 July - 21 July
includes taxes & fees
9.2/10 Wonderful! (1,378 reviews)
"We stayed at Harbor Shores for two nights and it was great! It’s literally across the street from the lake and a minutes walk from anywhere in downtown. The staff provided a list of suggestions on where to go for the best dining and each place we tried was excellent. The room was nice and had everything ..."

Reviewed on 13 July 2026

Harbor Shores on Lake Geneva
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is NZ$323 per night from 22 July to 23 July
NZ$323
22 July - 23 July
includes taxes & fees
9.2/10 Wonderful! (1,663 reviews)
"Such a fun stay, clean room and late night eats!"

Reviewed on 14 July 2026

Potawatomi Hotel & Casino
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is NZ$453 per night from 26 July to 27 July
NZ$453
26 July - 27 July
includes taxes & fees
9.6/10 Exceptional! (2,176 reviews)
"Our whole experience was fantastic. Check-in was quick and they offered champagne. The Bellhop that helped us with our luggage and finding our room was an absolute delight and the property was immaculate. Would love to visit again."

Reviewed on 13 July 2026

The Pfister Hotel
See all 2,464 properties in Southeast Wisconsin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Southeast Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.
Photo by Tim Ard
Open Photo by Tim Ard

American Family Field

9.0/10 (2,832 reviews)
Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
See properties

Frequently asked questions

How much does a Southeast Wisconsin holiday package cost?
Much less than you might think — from as low as NZ$3,234, as a matter of fact! By combining hotels, flights and car rentals into your own custom-made holiday package, your getaway to Southeast Wisconsin is just clicks away.
How do I get a cheap travel package to Southeast Wisconsin?
Bundle your flights and hotels, add on extras such as activities, and save with a Southeast Wisconsin holiday package. You won't just pick up exciting discounts on your adventure — you'll have lots of choice within your reach too. When you book through Expedia, you can select from more than 550 airlines and 1 000 000 hotels around the globe. Your next big adventure starts right here, right now!
Where should I stay in Southeast Wisconsin?
You'll fall in love with Milwaukee. Renowned sights, such as Milwaukee Art Museum and American Family Field, will keep you busy in this exciting city.
What are the top hotels in Southeast Wisconsin?
For hotels in Milwaukee with friendly service and comfy beds, you can't beat Potawatomi Hotel & Casino and Best Western Plus Milwaukee Airport Hotel & Conference Ctr. If you're visiting Lake Geneva as well, you can look forward to a solid night's sleep at Mt. Olympus Water & Theme Park Resort or Hilton Milwaukee City Centre.
How far in advance should I book my Southeast Wisconsin holiday?
Savvy travellers always book early. Air carriers typically release flight tickets up to 12 months prior to departure, and this is your chance to land some of the lowest prices. Boss just told you to use up your holiday time next month? That's fine too — Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Southeast Wisconsin travel package include?
That's up to you. You can choose from a range of Southeast Wisconsin bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Southeast Wisconsin trip looks like, get set to save!
What should I know before booking a Southeast Wisconsin travel package?
When you book your hotels, flights and car rentals together, you'll land awesome discounts. Whether you're organising a rural escape in a cottage or want to stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Southeast Wisconsin Expedia holiday package?
Definitely. Expedia has over 550 partner airlines to select from around the world. With so much choice, finding the right carrier to take you to Southeast Wisconsin will be a breeze.
If I'm not able to travel, can I cancel my Southeast Wisconsin holiday package?
It is possible to cancel your Southeast Wisconsin booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.